Dimethylamine → Allyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylate

HRID 52005Notes

Reaction equation

HRID 52005 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:12]2[C:13]([C:17](Cl)=[O:18])=[C:14]([CH3:16])[O:15][C:11]=2[CH:10]=[CH:9][C:8]=1[O:20][C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1)=[O:6])[CH:2]=[CH2:3].[CH3:31][NH:32][CH3:33].O>ClCCl>[CH3:30][O:29][C:23]1[CH:24]=[C:25]([O:27][CH3:28])[N:26]=[C:21]([O:20][C:8]2[C:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[C:12]3[C:13]([C:17](=[O:18])[N:32]([CH3:33])[CH3:31])=[C:14]([CH3:16])[O:15][C:11]3=[CH:10][CH:9]=2)[N:22]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 199627534-Allyloxycarbonyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride

Product 1

HCID 19962758Allyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-3-dimethylcarbamoyl-2-methylbenzofuran-4-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 g of 4-allyloxycarbonyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-methylbenzofuran-3-carbonyl chloride was dissolved in 13 ml of dichloromethane, and 1.5 g of a 50% dimethylamine aqueous solution was dropwise added thereto under cooling with ice. After stirring for 30 minutes, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The oily substance obtained by concentration under reduced pressure, was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 1.84 g (yield: 60%) of the desired compound.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe oily substance obtained by concentration under reduced pressure
  6. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-abbf02b268b9417598672fcd1e9af98a
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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